From Surf Wiki (app.surf) — the open knowledge base

Aziridine

Organic ring compound with the formula (CH2)2NH

Ethylenimine Aminoethylene Dimethyleneimine Dimethylenimine Ethylimine | NFPA-H = 4 | NFPA-F = 3 | NFPA-R = 3 56 ppm (rabbit, 2 hr) 250 ppm (guinea pig, 1 hr) 62 ppm (rat, 4 hr) 223 ppm (mouse, 2 hr) 56 ppm (rat, 2 hr) 2236 ppm (mouse, 10 min) Ethylene oxide Thiirane

Aziridine is an organic compound consisting of the three-membered heterocycle . It is a colorless, toxic, volatile liquid that is of significant practical interest. Aziridine was discovered in 1888 by the chemist Siegmund Gabriel. Its derivatives, also referred to as aziridines, are of broader interest in medicinal chemistry.

Structure

The bond angles in aziridine are approximately 60°, considerably less than the normal hydrocarbon bond angle of 109.5°, which results in angle strain as in the comparable cyclopropane and ethylene oxide molecules. A banana bond model explains bonding in such compounds. Aziridine is less basic than acyclic aliphatic amines, with a pKa of 7.9 for the conjugate acid, due to increased s character of the nitrogen free electron pair. Angle strain in aziridine also increases the barrier to nitrogen inversion. This barrier height permits the isolation of separate invertomers, for example the cis and trans invertomers of N-chloro-2-methylaziridine.

Synthesis and uses

Aziridine is produced industrially from aminoethanol via two related routes. The Nippon Shokubai process requires an oxide catalyst and high temperatures to effect the dehydration. In the Wenker synthesis, the aminoethanol is converted to the sulfate ester, which undergoes base-induced sulfate elimination. Older methods entailed amination of 1,2-dichloroethane and cyclization of 2-chloroethylamine.

Aziridine forms a wide variety of polymeric derivatives, known as polyethylenimines (PEI). These and related species are useful crosslinking agents and precursors for coatings.

Safety

Aziridine is highly toxic with an LD50 of 14 mg (oral, rats). It is a skin irritant. As an alkylating agent, it is also a mutagen.

References

(1999). "Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide".
Weast, Robert C.. (1978). "CRC Handbook of Chemistry and Physics". CRC Press.
{{PGCH. 0274
{{IDLH. 151564. Ethyleneimine
Gilchrist, T.L.. (1987). "Heterocyclic chemistry". Longman Scientific & Technical.
''Epoxides and aziridines – A mini review'' Albert Padwa, S. Shaun Murphree [[Arkivoc]] (JC-1522R) pp. 6–33 [http://www.arkat-usa.org/ark/journal/2006/I03_Coxon/1522/JC-1522R.asp Online article]
(2006). "Aziridines".
Gabriel, S.. (1888). "Ueber Vinylamin und Bromäthylamin. (II.)". Berichte der Deutschen Chemischen Gesellschaft.
(May 1995). "Occupational respiratory and skin sensitization caused by polyfunctional aziridine hardener". Clin Exp Allergy.
(2003). "Skin and respiratory allergic disease caused by polyfunctional aziridine". Med Lav.
Mapp CE. (2001). "Agents, old and new, causing occupational asthma". Occup. Environ. Med..

Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

functional-groups iarc-group-2b-carcinogens aziridines substances-discovered-in-the-19th-century

Want to explore this topic further?

Ask Mako anything about Aziridine — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report